The present invention relates to a compound which has been given the abbreviated name ITA 362.
The inventors succeeded in obtaining the said product ITA 362 for the first time in the course of a chemical and pharmacological study of new molecules of the general formula ##STR3## where R.sub.1 is methyl, phenyl or p-chlorophenyl, and R.sub.2, R.sub.3 hydrogen, alkyl, hydroxyalkyl, cycloalkyl, aryl, guanidin, dimethylguanidin. About sixty new molecules have been obtained in this work.
The search for chemical procedures which would make it possible to obtain the aforesaid compounds of the general formula VI was a very laborious and complicated one, since the unfavourable conditions of the reaction for obtaining the bromomethyl derivative of formula II ##STR4## required ample, extensive and difficult study. Specifically, the difficulty is due to the fact that it is necessary to use an excessive amount of epibromhydrine to bring about this reaction. The problem then arises that this reagent, i.e. the epibromhydrine, polymerizes and produces reaction mixtures which are very difficult to purify. To overcome these obstacles, it was necessary to find the combination of proportions, temperature, time and catalyst which would make it possible to obtain with only one distillation a product of sufficient quality to be used in the next reaction.
The said chemical research work was finally successful, in that synthesis was achieved of a large number of compounds of formula VI.
In view of the chemical structure of these formula VI compounds, the inventors hoped to discover interesting pharamacological properties in some of them. Specifically, the original design of formula VI was created by combining into a single molecule two structures which have been shown to possess good vasodilatory or anti-angina activity. One is the benzofuranic structure, common to drugs presently in use such as Amiodarone (Inventors: Touder, Bidon; U.S. Pat. No. 3,248,401) and Benziodarone (Inventors: Buu-Hoi, Beaudet; U.S. Pat. No. 3,012,042). The other structure is the dioxolanic rest, common to molecules being researched such as 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane (Researchers: Melson et col.; Acta Biol. Med. 395 (1961)), and which are also part of known drugs such as Guanadrel (Inventors: Hansson et col.; Clin.Pharmac.Therap. 14,204 (1973)).
With the described design of the molecule of formula VI, the inventors combined into a single molecule different pharmacological activities, namely: anti-arrhythmic, vasodilatory and anti-angina, which in conjunction with low toxicity could constitute a useful drug for treating the circulatory diseases, principally those affecting the heart.
The inventors have in fact succeeded in obtaining pharmacologically interesting formula VI products. For example, when R.sub.2, R.sub.3 is guanidin or dimethylguanidin, a group of compounds is obtained of such pharmacological importance that they were presented at the II National Congress of the Spanish Chemical Therapy Society, held in Madrid in 1982.
Accordingly, it is clear that the initial work of chemical nature attempting to achieve synthesis of formula VI products was begun with the clear intention of discovering interesting pharmacological properties in these products.
In this research process, the outstanding product in terms of its excellent pharmacological properties was the one called ITA 362, which is a formula VI product in which R.sub.1 is p-chlorophenyl, R.sub.2 is hydrogen and R.sub.3 is n-But, in other words, the product of formula I ##STR5## which is the object of this invention.